When Jake Cleland started out as a writer, he had nothing to lose. It was 2010 and street press was everywhere, and somewhere on a curb, the infancy of his work was printed on the pages of InPress and The Big Issue. Taking time to focus on community radio at SYN, Jake soon found a voice in music and pop criticism, reporting on everything from Dune Rats' secret house parties to reviewing records by Drake and The Black Keys.

Honing his skills at Everguide and TheVine to later become the editor-in-chief of the latter, Jake had begun branching out internationally, writing for publications like Pitchfork, the Sydney Morning Herald, and the Guardian. Contributing his opinions at BIGSOUND and Face The Music as an industry expert, Jake found the time to work on his own self-publishing project called STRINE WHINE, a monthly magazine that focused on Australian music and its artists. Years on and now teaching Entertainment Journalism at Collarts, Jake has since retired from the mag to focus on his own pursuits around technology, writing, and its intersections. We spoke to Jake about the highs and lows of freelancing, and why writing for yourself is an art many people can overlook.

Hey Jake, thanks for chatting with me! Working as a freelance journalist for over eight years, it’s safe to say you’ve had your run-in with pitching. What’s something you’re still learning every time you put together a piece? There’s never an easy way to write a conclusion. For the robot army Elon Musk is building to automate away all our jobs, this will be the toughest hurdle. I’ve also never figured out how to discern what the response to a piece will be. There’s an old saw that whatever you put the most effort into will go the most ignored; I’m pretty sure the most widely read piece of work I’ve ever published was a rehash on a TMZ report about Paul Walker’s death that I got up in about two minutes. Working in the 24-hour news cycle at TheVine (#RIP) was a great lesson in expecting the unexpected. When I was younger, this was frustrating! But it gets less frustrating when you learn to enjoy your own work and appreciate what other people take away from it separately.

"Writing fast, often, and with abandon is crucial. Without the close support of other writers though, that’s a pretty daunting prospect. The best thing you can do is be your own boss and roll deep."

Over the years, you’ve gained the representation of a writer, editor and critic in the Australian music community. What advice would you give those wanting to write about music but don’t know where to start? Please, please, start your own thing, and try to write with the intention of making your own writing stronger, not just to get door spots and pre-release streams. I’m still a little surprised that emerging writers haven’t taken the same initiative as musicians with how easy it is to publish and distribute now. Especially when you’re starting out as a writer, you have nothing to lose and everything to gain by venturing something bold, even (especially) if you’re wrong.

I can’t count the number of times I got brutally owned in the first few years of my career. All of them were important in helping me figure out how to communicate and sharpen my points. Writing fast, often, and with abandon is crucial. Without the close support of other writers though, that’s a pretty daunting prospect. The best thing you can do is be your own boss and roll deep.

In a recent review, you noted that ‘music writing is sadism and masochism.’ As someone who also writes about music, I think there’s truth in that. What ironies, roadblocks orideals do you feel young writers should be aware of? So that line and the point I was making around it is kind of the perfect example of an irony, a roadblock, and an ideal. The ideal is that music writing is communicating precisely how you feel. The irony is that, at the best of times, to me, that seems totally untenable! The roadblock that you have to overcome is not letting that stop you from trying. Uh, not to get into the semantic weeds too deep, but language is only a pretty facile doodle of meaning, and the noise gumming up the signal of what you’re actually trying to impart is lifetimes of personal biases and experiences that are impossible to extricate.

"The days of headline -> header image -> black text on a white page -> byline are dwindling."

Recently, you went back to university to study IT. How do you think technology and social media has changed the way we view writing and journalism? It typically seems pretty miserable, right? Obviously, the web has led countless industries to bottom out while new ventures have taken the opportunity to thrive. It’s an Ouroboros: my first favourite music publication was on the web (Idolator) but eventually fell to the post-aughts commercial imperatives of web publishing. Now with Facebook etc attempting to change news feed algorithms to promote “quality” content over so-called clickbait, I’m hoping we’ll see a paradigm shift where those commercial imperatives more closely align with stronger editorial.

There’s also promise in ventures like LNWY and Bandcamp Daily, where a festival or a tech music company runs an editorial wing which seems less burdened by the ad economy and takes advantage of that to publish some obscure but incredible stuff. And this environment also fosters what I was talking about above—the ability to start your own thing. The web gives us so many incredible tools to present journalism and we’re only just beginning to take advantage of them. The days of headline -> header image -> black text on a white page -> byline are dwindling.

With Twitter and other forms of social media now being used as reporting tools for journalists, the idea of a “Hot Take” could be seen as a double-edged sword. Do you think “Hot Takes” are good or problematic when it comes to writing? I’m sort of interested in how the concept of the “Hot Take” as something exceptional or note-worthy has died down. Like “oversharing” it’s become just another accepted part of how we converse online. I think hot takes are probably essential, but what I think is problematic is when a poorly considered hot take is defended by the author or publication as “starting a conversation.” The longer I’m a writer, the more I figure out which of my excuses are just cowardice in disguise. “I’m just trying to start a conversation” is one of them. And the older I get, the more I see the same conversations happening.

The people actually pushing the conversations forward now are usually activists or the people on the front lines of the issue —it’s almost never entertainment journalists any more. Look at how much folks like Camp Cope, LISTEN, and Jen Cloher have accomplished. They weren’t rich or influential when they started this work but over the past few years they’ve galvanised enough people to affect massive change. Australian music journalists should ask themselves why they couldn’t do the same thing. And it’s not entirely the fault of the journalists. I’m largely sympathetic to the modern editor, overworked and underpaid and probably writing a lot of the content on the site themselves. But more stringent editing is how we get hot takes developed into forward-thinking stories. Do more of that.

"Write about it like nobody is reading. Don’t write to get read! Write to get better! Does this sound gruelling and unglamorous? Writing is!"

You recently finished publishing STRINE WHINE, your monthly magazine focused on Australian music. For those wanting to publish their own independent magazine, what do you feel are the challenges of commissioning and editing others work? Not commissioning absolutely all of it is one of them. I got a lot of pitches when I was doing STRINE WHINE and they were uniformly great. This is another reason I wish more people would start their own thing. Those pitches should get published somewhere. They were so good. They were life-changingly good. They changed exactly zero lives because they weren’t published anywhere. But we were a pretty small operation and still consistently over budget and behind schedule so I turned down a lot of potentially great stories. The main challenge is not having ten million dollars. If you have ten million dollars, hit me up on Facebook. I mean, this is the main challenge of real life, right? Everyone with ten million dollars: you’re totally spending it on the wrong things!

"Hot takes and Twitter voices will come and go, but nothing will ever replace a journalist with a deep connection to their subject and community."

Teaching Entertainment Journalism at Collarts, what advice would you give those students wanting to make it as a freelance writer beyond their studies? I can’t repeat this enough: start your own thing. If you can get an internship to help teach you how a publication works from experience, all the better. But don’t get stuck as an intern; suss out whether it will actually turn into work, and if not, learn what you can and go work at a bar. Go work at a bar anyway. Try not to drink too much. Start working out. Learn how to cook something you can make a lot of and reheat through the week. Pay your rent and bills and spend all your time going out and then writing about it. Write about it like nobody is reading. Don’t write to get read! Write to get better! Does this sound gruelling and unglamorous? Writing is! Also, email me if you ever want advice. My email is jakecleland@gmail.com. I was (and still am!) the beneficiary of advice from older and much smarter people than me and I will be happy to pass off their wisdom as my own.